Welcome to the Windy City! Whether a local or a traveler eager to explore beyond the skyline, our guide to the best day trips from Chicago is your ticket to adventure. We’ll show you how to swap city streets for scenic escapes, all within a day’s reach of Chicago. From charming small towns to natural wonders, get ready to discover the Midwest’s most unforgettable experiences. Pack your sense of adventure, and let’s hit the road – Chicago-style day trips await!
Incredible Day Trips from Chicago
The city is ideally located with easy border-crossing into Wisconsin, Michigan, and Indiana. It is also a great starting point for a day trip further south into central Illinois. You have four states at your fingertips – so you should carve out time for a day trip while visiting.
1. Milwaukee, WI
If you want a fantastic day out from Chicago, Milwaukee is ideal. It has a strong sense of culture and many niche pockets of interest, like Harley-Davidson bikes and breweries. It is also a breeze to reach by train or car.
Distance from Chicago: 1.5 hours How to get there: Train, bus or coach
Suggested Tour: A Group Tour to Discover Milwaukee
2. South Bend, IN
South Bend is definitely slower-paced than quick-footed Chicago. However, it has lots of attractions too. Think of it as a relaxing and intellectual place to spend a day sightseeing. It has lots of fun and student twists, like cheap bars and coffee spots.
The city is located just east of Chicago, on the other side of Indiana Dunes National Park, and on the lower east shore of Lake Michigan. It is best reached by car, and we’d recommend stopping off at the national park en route.
Distance from Chicago: 2 to 3 hours How to get there: Car or train
3. Madison, WI
Madison is also beautifully located next to two huge lakes – Lake Mendota and Lake Waubesa. Summer leaves plenty of opportunities for water sports and sunny waterfront hiking trails. Follow this walking tour to see the city’s architecture including the State Capitol, Der Rathskaller, Bascomb Hill, and Memorial Union.
Distance from Chicago: 2 to 4 hours How to get there: By car or shuttle bus
4. Starved Rock State Park, IL
Nature lovers will adore this day trip choice. Not only is the natural scenery astounding, but you can also spot wildlife like white-tailed deer and bald eagles. Starved Rock State Park covers over 2,600 acres and has 13 miles of trails, with 18 canyons to admire. It is located inland from Chicago and Lake Michigan.
Distance from Chicago: 1.5 hours How to get there: Car
5. Cedarburg, WI
Cedarburg has serious charm. It has old-school-style houses and is frequently compared to a movie set. The town was founded in the 1840s by a mixture of predominantly Irish and German settlers and is now considered a suburb of Milwaukee. Cedarburg has many cute and aesthetic things to do, with the bonus of brewery and winery tours. You can walk the vineyards and tour brewing rooms or head to unique attractions like the Wisconsin Museum of Quilts and Fine Arts. Cedarburg is a real gem and beats to its own drum, making it a memorable day trip from Chicago.
This Wisconsin town is located just north of Milwaukee’s city center. It is best reached from Chicago by car, and you can always incorporate a stop-off in Milwaukee’s city center – parking in the outskirts and commuting in.
Distance from Chicago: 2 hours How to get there: By car
6. Illinois Beach State Park, IL
It has campgrounds and playgrounds, plus shower blocks and a nature center. Illinois Beach State Park is somewhere to spend an entire day. Start with a hike and visit the nature center before heading to Isherwood Beach, and even camping overnight if your schedule allows it.
The park is quite close to Chicago, taking less than an hour to reach by car. It’s a great day trip if you have a warm day or fancy a beach trip. Or it is the perfect adventure if you fancy camping a night to break up your classic city break.
Distance from Chicago: 1 hour How to get there: By car
7. Lake Geneva, WI
Once you arrive, you are greeted by Gilded Age mansions with dramatic architecture and a scenic Shore Path that snakes around the city’s section of Geneva Lake. Historically, Lake Geneva was used as a bolt-hole for affluent Chicago residents, and looking at the city’s surrounding natural beauty, it’s easy to see why.
Admire Victorian history and Gilded Age architecture, and visit the Lake Geneva beaches. Big Foot Beach State Park has brilliant beaches, especially for a lazy afternoon. Lake Geneva is a beautiful day trip destination to unwind before revisiting Chicago’s chaotic sightseeing scene.
Distance from Chicago: 1.5 hours How to get there: By car
8. Rockford, IL
Rockford is located in northern Illinois, right under the Wisconsin border. We’d recommend combining it with a trip to Madison, located roughly an hour above the city. It is a great stop-off point for those driving to the Wisconsin capital.
Distance from Chicago: 1.5 hours How to get there: By car
9. Indiana Dunes National Park, IN
Indiana Dunes National Park is located just southeast of Chicago and is ideally combined with visits to South Bend or day trips into Michigan or Indiana.
Distance from Chicago: 50 minutes How to get there: By car
10. Lakeshore State Park, WI
The state park is obviously well combined with a visit to Milwaukee. This little island state park is a beautiful spot near the city. It is located off the Historic Third Ward and accessible by a pedestrianized bridge connecting it to the mainland.
Distance from Chicago: 1.5 hours How to get there: By car
11. Monroe, WI
Monroe is pretty cool. The quirky city is known as the Swiss cheese capital. It has a vast history of dairy farming that has given it a massive cheese reputation. You can visit to take food tours – highly recommended – and try local products and produce. You should visit the National Historic Cheese Making Center Museum and the Chalet Cheese Cooperative. There’s also beautiful architecture and historic places, like the Green County Courthouse, completed in 1891. The Monroe Historic Square is in the city’s center, surrounded by shops and aesthetic scenery.
Monroe is a tiny city compared to some of Chicago’s neighboring giants. It is roughly located halfway between Madison and Rockford. It is definitely best accessed by car.
Distance from Chicago: 2 hours How to get there: By car
12. St. Joseph, MI
St Joseph is a beautiful choice if you want one of those traditional seaside day trips. It is only a short drive from Chicago, despite the fact that you’ll be venturing through Indiana and crossing the Michigan border. Hooray for Lake Michigan’s close network of US states. It is fantastic to combine with Indiana Dunes National Park and Michigan City.
Distance from Chicago: 1.5 hours How to get there: By Car
13. Channahon State Park, IL
You can organize guided tours around Channahon State Park, including canoe trips. The state park is a designated part of the Illinois and Michigan Canal National Heritage Corridor. It is widely hailed as an essential part of the state’s history. It is a nature-given adventure park.
Distance from Chicago: 50 minutes How to get there: By car
14. Oak Park, IL
It is so handy to jump on a train and be amongst dozens of museums. Additionally, its Unity Temple was recently designated as a UNESCO World Heritage in 2019. Despite all its existing attractions and offerings, Oak Park is very much up and coming in terms of visitor recognition and value for tourism.
Distance from Chicago: 15 to 20 minutes How to get there: By train
15. Grand Rapids, MI
We like to catch a shuttle to Grand Rapids, as it has an illustrious brewery history. In particular, it is known for New Holland Brewing, and you can take guided tasting tours at the local breweries that are still running. Otherwise, driving is quicker, and you can stop off at spots like Indiana Sand Dunes National Park, St Joseph, and South Bend. You hug the lower shoreline of Lake Michigan, which is a long but very scenic drive. Ideally, rotate drivers and have a few different stops en route.
Distance from Chicago: 3 to 5 hours How to get there: By car in just under 3 hours or by shuttle in under 4 Suggested Tour: Grand Rapids Ghost Tour
16. Windmill Island Gardens, MI
This is one of the leading day trips from Chicago if you want Dutch heritage, and it is even located outside of a city named Holland. Windmill Island Gardens is located in Michigan, so you’ll be driving the south coast of Lake Michigan, cutting through northern Indiana and across the Michigan border. When it comes to visiting Michigan, distance can be a concern. Is it a long day of driving? Yes. But it is incredibly scenic and a great way to combine several attractions. If you have a few drivers, you won’t have any trouble as you can just rotate driving time.
Distance from Chicago: 2.5 hours How to get there: By car
17. Galena, IL
Galena is right in the top left corner of Illinois, on the border of Iowa and Wisconsin. It is a fabulous add-on from Rockford or Starved Rock State Park, around 1.5 hours away by car.
18. Michigan City, IN
There’s also period history at the Barker Mansion, which showcases English-inspired decor and furnishings in a 19th-century mansion. Admire the history, have a beach day, or enjoy inner-city shopping at outlet stores. Michigan City offers loads and, at the very least, is a change of scene.
You can easily visit Michigan City; proper day-long trips are low on travel time and high on attractions. And that sums up this lakeside city.
Distance from Chicago: 1 to 2 hours How to get there: 1 hour by car or 2 hours by train
19. Peoria, IL
Peoria has beautiful riverside parks, including Peoria Riverfront Park and Liberty Park. There’s also the Riverfront Museum and Peoria Historical Society. It is a lovely place to just walk and explore on foot. And the contrast between hectic Chicago and sedate Peoria is vast, making it a worthwhile day trip.
The city is located southwest of Chicago and is best accessed by car. This way, you can also stop off at Starved Rock State Park on the way.
Distance from Chicago: 2.5 hours How to get there: By car
20. Six Flags Great America, IL
Everyone loves a fun day out. And Six Flags Great America is the perfect day trip to skip sightseeing and escape the city to enjoy some quality ‘fun’ time. It is the ideal place to let your hair down and has an impressive range of rides, making it suitable for adults and children. Six Flags Great America is located north of Chicago, just under the Wisconsin border. Get your tickets in advance here.
Distance from Chicago: 1 to 2 hours How to get there: 1 hour by car or 2 hours by train then bus
21. Glacial Park Conservation Area
Glacial Park Conservation Area opens from sunrise until sunset all year round. It is ideal if you want to switch from the standard suburban park experience to a bit of rugged, remote nature.
Distance from Chicago: 1 hour and 20 minutes How to get there: By car
Are you looking for more inspiration? Why not check out our guides on the best things to do in Wisconsin and the best places to visit in Michigan? We’ve also got notes on the best, most unique things to do in Northern Michigan specifically, so check that out if you have time to add a couple of days to the end of your Chicago trip. If you have longer, why not take a 2-3 day excursion from Chicago? It is a brilliant launchpad to discover more of the experiences in the states around Lake Michigan. Chicago’s location is by far its winning quality, and you should take advantage of it when planning day trips and excursions.
